Book Luxury Short Stay Rentals in Old Windsor

We selected the best homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights

Island Tides

Island Tides

  • 8 guests

  • 4 bedrooms

England, United Kingdom

Connected to the mainland by a tombolo, the isle of Portland is a pretty spot off the Dorset Coast. This chic house is in the village of Fortuneswell in the north of the island, and it makes the perfect place to begin your adventures.

It’s for the Birds

It’s for the Birds

  • 8 guests

  • 4 bedrooms

Westbury, Buckinghamshire

This secluded mansion has an owl barn and a dovecote, and plays host to red kites, herons, barn owls, mallard and many smaller feathered friends; it really is 'for the birds'. Perfect for large families or groups of friends looking for a rural escape, this is a fun-filled countryside haven.

Wooden Shoes

Wooden Shoes

  • 2 guests

  • 1 bedrooms

Cromer, Norfolk

Quaint and cosy, this old shoemaker's cottage in the heart of Cromer is a perfect seaside retreat for two. It's just a two-minute walk from Cromer Beach and the Victorian pier, making it a top-notch spot for couples to unwind.

Serving Up Style

Serving Up Style

  • 4 guests

  • 2 bedrooms

Wimborne Saint Giles, Wimborne

Part of a nineteenth-century groom’s cottage on the grounds of St Giles House in Dorset, this maisonette in a former stable block looks like a scene straight out of Bridgerton. A stylish mishmash of antique brickwork, vintage pieces and modern design touches, every inch has been cleverly renovated by Lord and Lady Shaftesbury to enhance the history and character in an uber-cool way.


We selected the top 3% holiday homes in Old Windsor Short Stay Rentals

Explore the 3 most perfect homes in our collection

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Most popular homes

Into the Forest

Into the Forest

  • 5 guests

  • 2 bedrooms

Burley, Hampshire

Fosse Way

Fosse Way

  • 4 guests

  • 2 bedrooms

Kingsbury Episcopi, Martock

Mane Character

Mane Character

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

Where Skylarks Sing

Where Skylarks Sing

  • 4 guests

  • 2 bedrooms

Tunstead Milton, High Peak

Pause For Thought

Pause For Thought

  • 4 guests

  • 2 bedrooms

Chester, Cheshire West and Chester

Dovesong

Dovesong

  • 6 guests

  • 3 bedrooms

Weston Subedge (DET), Gloucestershire

The Rocking Stone

The Rocking Stone

  • 4 guests

  • 2 bedrooms

Matlock, Derbyshire

Wink to the Past

Wink to the Past

  • 4 guests

  • 2 bedrooms

Hugill, Westmorland and Furness

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Old Windsor, England, United Kingdom. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Old Windsor luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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